Methyl indole-3-carboxylate → Methyl 1-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-1H-indole-3-carboxylate

HRID 455030Notes

Reaction equation

HRID 455030 reaction equation
N1(CC2N3C=C(C)C=CC3=NC=2C2C=CC(C)=CC=2)C=CN=C1.Cl.Cl[CH2:26][C:27]1[N:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]2=[N:29][C:28]=1[C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1.[NH:43]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[C:45]([C:52]([O:54][CH3:55])=[O:53])=[CH:44]1>>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([C:28]2[N:29]=[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]3[C:27]=2[CH2:26][N:43]2[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:45]([C:52]([O:54][CH3:55])=[O:53])=[CH:44]2)=[CH:37][CH:38]=1

Participants

4

Reactant 3

HCID 589098Methyl indole-3-carboxylateHCID 583370713-((1H-imidazol-1-yl)methyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridineHCID 670287193-(Chloromethyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine hydrochloride

Product 1

HCID 67028660Methyl 1-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-1H-indole-3-carboxylate

Procedure

The title compound was prepared according to Method A and the experimentals described for compound 1 from 3-(chloromethyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine hydrochloride and methyl 1H-indole-3-carboxylate. M/e+ 430 for C25H21ClN3O2 (M+H)+; 1H-NMR (400 MHz, CDCl3) δ 8.24 (dd, J=5.8, 2.5 Hz, 1H), 7.74 (d, J=9.1 Hz, 2H), 7.66 (d, J=8.4 Hz, 1H), 7.64 (m, 1H), 7.51 (s, 1H), 7.48 (m, 1H), 7.42 (d, J=8.4 Hz, 2H), 7.31 (m, 2H), 7.29 (t, J=5.8 Hz, 1H), 6.80 (t, J=6.9 Hz, 1H), 5.67 (s, 2H), 3.83 (s, 3H) ppm.

Sources & evidence

ORD record
ord-9228fa87a5e54aefb95f31f2cfe0ad5c
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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